ES2256052T3 - Nuevos derivados de benzimidazol utiles como agentes antiproliferativos. - Google Patents
Nuevos derivados de benzimidazol utiles como agentes antiproliferativos.Info
- Publication number
- ES2256052T3 ES2256052T3 ES00971654T ES00971654T ES2256052T3 ES 2256052 T3 ES2256052 T3 ES 2256052T3 ES 00971654 T ES00971654 T ES 00971654T ES 00971654 T ES00971654 T ES 00971654T ES 2256052 T3 ES2256052 T3 ES 2256052T3
- Authority
- ES
- Spain
- Prior art keywords
- benzoimidazol
- quinolin
- methoxy
- piperidin
- ethoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title claims description 9
- 230000001028 anti-proliverative effect Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 372
- 150000003839 salts Chemical class 0.000 claims abstract description 70
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 68
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 48
- 229940002612 prodrug Drugs 0.000 claims abstract description 34
- 239000000651 prodrug Substances 0.000 claims abstract description 34
- 125000004429 atom Chemical group 0.000 claims abstract description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 28
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 24
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 17
- 239000012453 solvate Substances 0.000 claims abstract description 15
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 11
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 8
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract description 4
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 165
- 239000002253 acid Substances 0.000 claims description 148
- 150000002148 esters Chemical class 0.000 claims description 74
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 34
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 32
- 241000124008 Mammalia Species 0.000 claims description 26
- 206010028980 Neoplasm Diseases 0.000 claims description 26
- 150000004702 methyl esters Chemical class 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 230000002159 abnormal effect Effects 0.000 claims description 20
- 201000011510 cancer Diseases 0.000 claims description 18
- DEEOXSOLTLIWMG-UHFFFAOYSA-N 1-[2-[5-(2-methoxyethoxy)-1-benzimidazolyl]-8-quinolinyl]-4-piperidinamine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 DEEOXSOLTLIWMG-UHFFFAOYSA-N 0.000 claims description 17
- BCRKZBOQBMOOKE-UHFFFAOYSA-N 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 BCRKZBOQBMOOKE-UHFFFAOYSA-N 0.000 claims description 16
- YNGYWZGVAHWYKA-UHFFFAOYSA-N 2-[5-(2-methoxyethoxy)benzimidazol-1-yl]-8-[4-(pyrrolidin-1-ylmethyl)phenyl]quinoline Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1CCCC1 YNGYWZGVAHWYKA-UHFFFAOYSA-N 0.000 claims description 14
- 230000010261 cell growth Effects 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- BVEMGSLZVMDRAU-UHFFFAOYSA-N 2-[5-(2-methoxyethoxy)benzimidazol-1-yl]-8-piperazin-1-ylquinoline Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCNCC1 BVEMGSLZVMDRAU-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 11
- RUPVQNDWKLBVDU-UHFFFAOYSA-N 1-[[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]methyl]pyrrolidin-3-ol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1CCC(O)C1 RUPVQNDWKLBVDU-UHFFFAOYSA-N 0.000 claims description 10
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- ZAPFTIBEIKCAKS-UHFFFAOYSA-N 2-(5-methoxybenzimidazol-1-yl)quinoline-8-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(N3C4=CC=C(C=C4N=C3)OC)=CC=C21 ZAPFTIBEIKCAKS-UHFFFAOYSA-N 0.000 claims description 9
- 230000012010 growth Effects 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- GQQCLFHJSQYYRZ-SFHVURJKSA-N (2s)-2-amino-1-[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperazin-1-yl]propan-1-one Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCN(C(=O)[C@H](C)N)CC1 GQQCLFHJSQYYRZ-SFHVURJKSA-N 0.000 claims description 7
- IDCRQLNHZFWXQL-VSGBNLITSA-N (3r,4r)-1-[[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]methyl]pyrrolidine-3,4-diol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1C[C@@H](O)[C@H](O)C1 IDCRQLNHZFWXQL-VSGBNLITSA-N 0.000 claims description 7
- BOSNLMMFMCANGE-UHFFFAOYSA-N 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidine-4-carboxylic acid Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(C(O)=O)CC1 BOSNLMMFMCANGE-UHFFFAOYSA-N 0.000 claims description 7
- MSEZXYYREBXKOC-UHFFFAOYSA-N 1-[2-[5-(cyclopropylmethoxy)benzimidazol-1-yl]quinolin-8-yl]-n-methylpiperidin-4-amine Chemical compound C1CC(NC)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC5CC5)C=C4N=C3)N=C12 MSEZXYYREBXKOC-UHFFFAOYSA-N 0.000 claims description 7
- UHFSUALOJAJWEA-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-ol Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(O)(CN(C)C)CC1 UHFSUALOJAJWEA-UHFFFAOYSA-N 0.000 claims description 7
- DSOPCJDOYLTEAH-UHFFFAOYSA-N 1-[1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-yl]-n-methylmethanamine Chemical compound C1CC(CNC)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCCOC)C=C4N=C3)N=C12 DSOPCJDOYLTEAH-UHFFFAOYSA-N 0.000 claims description 6
- JNKNUAUYOLHBEI-UHFFFAOYSA-N 1-[2-(5,6-dimethoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 JNKNUAUYOLHBEI-UHFFFAOYSA-N 0.000 claims description 6
- TWLLKADWWLFSJJ-UHFFFAOYSA-N 1-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 TWLLKADWWLFSJJ-UHFFFAOYSA-N 0.000 claims description 6
- ZJMUYOGWSXPZEC-UHFFFAOYSA-N 1-[2-(5-phenylbenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(C=C4N=C3)C=3C=CC=CC=3)N=C12 ZJMUYOGWSXPZEC-UHFFFAOYSA-N 0.000 claims description 6
- JJBQCMXPAWDJTC-UHFFFAOYSA-N 1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]-4-methylpiperidin-4-amine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(C)(N)CC1 JJBQCMXPAWDJTC-UHFFFAOYSA-N 0.000 claims description 6
- HHETXDYOEYLLRG-UHFFFAOYSA-N 1-[2-[5-(3-aminopropoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1=NC2=CC(OCCCN)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 HHETXDYOEYLLRG-UHFFFAOYSA-N 0.000 claims description 6
- HIEZOGPUHPBCLN-UHFFFAOYSA-N 1-[2-[5-(4-methoxyphenyl)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(C=N2)C=3N=C4C(N5CCC(N)CC5)=CC=CC4=CC=3)C2=C1 HIEZOGPUHPBCLN-UHFFFAOYSA-N 0.000 claims description 6
- GJHVPIXOGJZNNP-UHFFFAOYSA-N 1-[2-[5-(cyclopropylmethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC5CC5)C=C4N=C3)N=C12 GJHVPIXOGJZNNP-UHFFFAOYSA-N 0.000 claims description 6
- FPNNXTVDMZIKFS-UHFFFAOYSA-N 1-[2-[5-(pyridin-2-ylmethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC=5N=CC=CC=5)C=C4N=C3)N=C12 FPNNXTVDMZIKFS-UHFFFAOYSA-N 0.000 claims description 6
- ZZHQDJNRIHLNIC-UHFFFAOYSA-N 1-[2-[5-[3-(dimethylamino)propoxy]benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1=NC2=CC(OCCCN(C)C)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 ZZHQDJNRIHLNIC-UHFFFAOYSA-N 0.000 claims description 6
- JMPFBJJAPZNSIH-UHFFFAOYSA-N 1-[8-(4-aminopiperidin-1-yl)quinolin-2-yl]benzimidazol-5-ol Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(O)C=C4N=C3)N=C12 JMPFBJJAPZNSIH-UHFFFAOYSA-N 0.000 claims description 6
- GBWNEGOGPYFPLH-UHFFFAOYSA-N 1-[8-(4-aminopiperidin-1-yl)quinolin-2-yl]benzimidazole-5-carboxylic acid Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(C=C4N=C3)C(O)=O)N=C12 GBWNEGOGPYFPLH-UHFFFAOYSA-N 0.000 claims description 6
- WOQQQSUPCAHCFH-UHFFFAOYSA-N 4-(aminomethyl)-1-[2-[5-(pyridin-2-ylmethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-ol Chemical compound C1CC(CN)(O)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC=5N=CC=CC=5)C=C4N=C3)N=C12 WOQQQSUPCAHCFH-UHFFFAOYSA-N 0.000 claims description 6
- JMRIHUUTAOOKNK-UHFFFAOYSA-N 4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(O)C=C1 JMRIHUUTAOOKNK-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- UXJGHQQHEIIFAO-UHFFFAOYSA-N [1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-yl]methanol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(CO)CC1 UXJGHQQHEIIFAO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- RUPVQNDWKLBVDU-XMMPIXPASA-N (3r)-1-[[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]methyl]pyrrolidin-3-ol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1CC[C@@H](O)C1 RUPVQNDWKLBVDU-XMMPIXPASA-N 0.000 claims description 5
- IDCRQLNHZFWXQL-HNRBIFIRSA-N (3s,4r)-1-[[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]methyl]pyrrolidine-3,4-diol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1C[C@H](O)[C@H](O)C1 IDCRQLNHZFWXQL-HNRBIFIRSA-N 0.000 claims description 5
- DWNNTUUIPKZWOZ-UHFFFAOYSA-N 1-[1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-yl]-n,n-dimethylmethanamine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(CN(C)C)CC1 DWNNTUUIPKZWOZ-UHFFFAOYSA-N 0.000 claims description 5
- AWXYFYFBKOXFSQ-UHFFFAOYSA-N 1-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]-n,n-dimethylpiperidin-4-amine Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N(C)C)CC1 AWXYFYFBKOXFSQ-UHFFFAOYSA-N 0.000 claims description 5
- YCYUUTPEQGVZNM-UHFFFAOYSA-N 1-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-one Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(=O)CC1 YCYUUTPEQGVZNM-UHFFFAOYSA-N 0.000 claims description 5
- MMYDEBFLRLVECR-UHFFFAOYSA-N 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]-n,n-dimethylpiperidin-4-amine Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N(C)C)CC1 MMYDEBFLRLVECR-UHFFFAOYSA-N 0.000 claims description 5
- LHDXMKIZLCGVIL-UHFFFAOYSA-N 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]-n-methylpiperidin-4-amine Chemical compound C1CC(NC)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OC)C=C4N=C3)N=C12 LHDXMKIZLCGVIL-UHFFFAOYSA-N 0.000 claims description 5
- ACGUZOBLJIIJSZ-UHFFFAOYSA-N 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-one Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(=O)CC1 ACGUZOBLJIIJSZ-UHFFFAOYSA-N 0.000 claims description 5
- INBYXZYOANPYLM-UHFFFAOYSA-N 1-[2-(5-pyridin-3-ylbenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(C=C4N=C3)C=3C=NC=CC=3)N=C12 INBYXZYOANPYLM-UHFFFAOYSA-N 0.000 claims description 5
- QPTCRSKAQPYXRX-UHFFFAOYSA-N 1-[2-(5-pyridin-4-ylbenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(C=C4N=C3)C=3C=CN=CC=3)N=C12 QPTCRSKAQPYXRX-UHFFFAOYSA-N 0.000 claims description 5
- SJRWBGNQLJNBIJ-UHFFFAOYSA-N 1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]-n-(pyridin-3-ylmethyl)piperidin-4-amine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N(CC1)CCC1NCC1=CC=CN=C1 SJRWBGNQLJNBIJ-UHFFFAOYSA-N 0.000 claims description 5
- LWSBNWLLDYXSGC-UHFFFAOYSA-N 1-[2-[5-(3-methoxyphenyl)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound COC1=CC=CC(C=2C=C3N=CN(C3=CC=2)C=2N=C3C(N4CCC(N)CC4)=CC=CC3=CC=2)=C1 LWSBNWLLDYXSGC-UHFFFAOYSA-N 0.000 claims description 5
- WSHPGNLRMOQYGC-UHFFFAOYSA-N 1-[2-[5-(6-methoxypyridin-3-yl)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N(C=N2)C=3N=C4C(N5CCC(N)CC5)=CC=CC4=CC=3)C2=C1 WSHPGNLRMOQYGC-UHFFFAOYSA-N 0.000 claims description 5
- IAFYSPXKLJSJPA-UHFFFAOYSA-N 1-[2-[5-(pyridin-3-ylmethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC=5C=NC=CC=5)C=C4N=C3)N=C12 IAFYSPXKLJSJPA-UHFFFAOYSA-N 0.000 claims description 5
- XROUPEKOUWUJQC-UHFFFAOYSA-N 1-[2-[5-(pyridin-4-ylmethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC=5C=CN=CC=5)C=C4N=C3)N=C12 XROUPEKOUWUJQC-UHFFFAOYSA-N 0.000 claims description 5
- WXZRIHBJAUPFMW-UHFFFAOYSA-N 1-[2-[5-[2-(dimethylamino)ethoxy]benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1=NC2=CC(OCCN(C)C)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 WXZRIHBJAUPFMW-UHFFFAOYSA-N 0.000 claims description 5
- IJZNZDAHGOCSOM-UHFFFAOYSA-N 1-[2-[5-[4-(aminomethyl)phenyl]benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1=CC(CN)=CC=C1C1=CC=C(N(C=N2)C=3N=C4C(N5CCC(N)CC5)=CC=CC4=CC=3)C2=C1 IJZNZDAHGOCSOM-UHFFFAOYSA-N 0.000 claims description 5
- QEKDOMNEJOSDAR-UHFFFAOYSA-N 1-[4-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]phenyl]-n,n-dimethylmethanamine Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(CN(C)C)C=C1 QEKDOMNEJOSDAR-UHFFFAOYSA-N 0.000 claims description 5
- PQJHEPRSJAIZJL-UHFFFAOYSA-N 1-[4-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]phenyl]-n-methylmethanamine Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(CNC)C=C1 PQJHEPRSJAIZJL-UHFFFAOYSA-N 0.000 claims description 5
- ZBVXRRVOZXKWDG-UHFFFAOYSA-N 1-[4-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]phenyl]-n,n-dimethylmethanamine Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(CN(C)C)C=C1 ZBVXRRVOZXKWDG-UHFFFAOYSA-N 0.000 claims description 5
- RZIWPOGNSBXHPA-UHFFFAOYSA-N 1-[4-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]phenyl]-n-methylmethanamine Chemical compound C1=CC(CNC)=CC=C1C1=CC=CC2=CC=C(N3C4=CC=C(OC)C=C4N=C3)N=C12 RZIWPOGNSBXHPA-UHFFFAOYSA-N 0.000 claims description 5
- QBUAJCWWXANPTG-UHFFFAOYSA-N 1-[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]-n,n-dimethylmethanamine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(CN(C)C)C=C1 QBUAJCWWXANPTG-UHFFFAOYSA-N 0.000 claims description 5
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